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How To Become A Millionaire In All Areas Of Your Life

The Millionaire Mindcast is a show that focuses on all things mindset, money, and motivation to help aspiring millionaires from all walks of life increase their income, impact, and influence.

I’m Matt Aitchison - a 7-figure real estate investor, millennial entrepreneur, speaker and educator - and every Monday I interview a badass millionaire or thought leader who is living the "Whole Life Millionaire" lifestyle and taking their wealth far beyond what dollars can buy.

Join me each week for new insights as you march toward that million-dollar milestone and design your dream life. It's time to define what true wealth means to you, make your money matter, and unleash your millionaire within.

Sep 30, 2019

In this episode of the Millionaire Mindcast, Steve Olsher shares his entrepreneurial journey, the story behind his business, his breakdown and breakthrough moments, the lessons he learned in his entrepreneurial journey, and tips to avoid those tribulations!

Steve Olsher is a Founder/CEO of Latatud, Founder/Chairman of, is the premier online mixology and cocktail culture-related destination for men and women over the age of 21. Steve is a New Media Influencer, Creator of The New Media Summit, Host of Reinvention Radio and Beyond 8 Figures, NYT Bestselling Author, and Keynote Speaker.

Even back then, Steve had done his fair share of entrepreneurial endeavors like selling speakers out of the back of the van, and more. At the age of 19, he opens his own none liquor nightclub though his family has been in the liquor business since 1939. Later on, Steve jumped into their family business and figured out what he can do to develop it. He applied a lot of strategies, brought it into the online space, build their own brand, and build an e-commerce site from scratch.

Their business went smoothly until they experience the shaky moment where Steve had no choice but to walk away from it, sold everything in their family business, and manage the pain. Steve’s motivation in money helped him finds a way to recover everything he had lost. This opens up the door for him in real estate. He started buying, flipping, and selling homes. Steve turns his creativity into cash.

Despite his busy career, Steve didn’t forget to add value to other people and contribute something to the community through the lessons he learned so much over the years of his entrepreneurial career. Steve feels like it’s a call for him to help some of the folks to avoid all of those trials and tribulations he experienced.  Then, he decided to write a book and got into coaching, speaking space, and podcasting space. Steve founded the New Media Summit where he teaches people what he knows works and doesn’t work. Helping people become clear and articulating who they are and what they do. 


Some Questions I Ask:

  • What have you been up to since your last hang out here? (01:27)
  • What was the worst entrepreneurial thing you’ve done? (03:38)
  • How did you kind of stumbling into the online world? (04:20)
  • As you guys start to get more and more into the online space, tell me how came about? (08:36)
  • Did you know that you had stumbled across an opportunity or like what was your business strategy behind all of that? (11:09)
  • What did you learn at that moment that you have kind of carried on with you and the business moving forward? (15:00)
  • How did you get through that moment in time of 9 years of hard work turns into nothing? (18:23)
  • Did you completely turn your back away from and the whole family business and just go further in the real estate? (25:58)
  • How did you transition into the media world like podcasting and New Media Summit? (34:40)
  • What do you see a lot of people missing on that side of the business plan about ‘WHAT’? (39:35)
  • Tell me more about the New Media Summit. (42:01)
  • 3 things that measure your business’ success. (43:10)

In This Episode, You Will Learn:

  • The internet days look like during the ‘90s. (08:42)
  • Some key mistakes that they did in business. (13:13)
  • The moment where Steve walks away from the opportunity. (13:49)
  • Tips on how to make the best decision. (07:10)
  • How Steve got into the real estate space. (22:26)
  • The core questions to find your ‘What Framework’. (40:07)


  • “I’ve always been wired as an entrepreneur.”
  • “We’re better than we did.”
  • “No one can raise your baby like you can.”
  • “Your business is your baby.”
  • “Just be really clear on why you’re doing something.”
  • “Look at if there are better ways potentially to get to whatever that destination.”
  • “You need to be money motivated.”
  • “There are a lot of opportunities here in this world of real estate.”
  • “You should be able to turn every visibility, opportunity into revenue.”

Resources Mentioned:

Connect with Steve Olsher on:


Reinvention Radio Podcast

New Media Summit